Windmill Lounge

While some places strive to be a dive, this quirky booze filled oasis, hidden down a sketchy stretch of Maple Avenue-- is the epitome of one. And as such, it's one of the most beloved cocktail havens in town, and perhaps, even in the country. But don't take our word for it, take Esquire magazine's-- which ranked it among the Best Bars in America in 2013. Sporting a neon windmill on the roof and a decidedly no-frills decor, complete with the requisite jukebox banging out Iggy Pop and Sinatra, the Windmill Lounge is a veritable outpost of cool. It's also the kind of place where everyone is friends, the drinks are sensational and the bartenders are having as good a time as the guests. Another reason to head here? The place puts on the best karaoke nights (held on Thursdays) in town.